Conversations are a two way street. A real conversation involves both sides. And it can simply be hard to get that street opened up due to age gap, authority, gender, whatever.

I think the heart of the OP is that if someone is trying to open up on their side, and this is a person who you would like to talk to/know, then you should take advantage of the opportunity to talk /listen while you have it.

Now it may turn out (or you may already know) that that street has nothing but pain. In that case, of course, there is far less of a reason to.